CN1976968A - Flexible, impact resistant primer - Google Patents
Flexible, impact resistant primer Download PDFInfo
- Publication number
- CN1976968A CN1976968A CNA2005800215604A CN200580021560A CN1976968A CN 1976968 A CN1976968 A CN 1976968A CN A2005800215604 A CNA2005800215604 A CN A2005800215604A CN 200580021560 A CN200580021560 A CN 200580021560A CN 1976968 A CN1976968 A CN 1976968A
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- Prior art keywords
- urethane
- epoxy
- component
- polyepoxide
- organic compound
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/58—Epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/12—Polycondensates containing more than one epoxy group per molecule of polycarboxylic acids with epihalohydrins or precursors thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
- Polyurethanes Or Polyureas (AREA)
- Materials For Medical Uses (AREA)
- Luminescent Compositions (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Joining Of Building Structures In Genera (AREA)
Abstract
A two-component epoxy amine primer system is disclosed. The epoxy component comprises an epoxy functional extended urethane, particularly one having one or more bisphenol components.
Description
Invention field
The present invention relates to the improved priming paint that contains Resins, epoxy-amine.
Background information
Resins, epoxy-amine coating, especially chromate-containing those, in aircraft industries, be used as the priming paint of paint.Priming paint provides and forms strong agglutinating middle layer with metallic surface (normally aluminium) and provide the finishing coat can agglutinating outside surface strong with it.Except to the adhering to of finishing coat, priming paint also is used for resisting the corrosion to underlying metal.This erosion resistance not only comprises the ability of the metallic surface that protection is covered by priming paint, and comprises and extend to this protection outside the edge of this primer coating and prevent that adjacent uncoated surface is subjected to the corrosive ability.Consider the various corrosive fluids that use in this industry for example rocket engine fuel, braking fluid etc., this especially should pay close attention to.Wishing also that this type of priming paint has enough flexiblely is exposed to severe cold under it to resist aircraft.Shock resistance also wishes, this equally especially should pay close attention to consider noise that aircraft stands and vibration.
Summary of the invention
The present invention relates to the urethane and the purposes in two component epoxy/amine paint base system thereof of epoxy functional extended.Compare with other Resins, epoxy-amine priming paint, have improved flexible, shock resistance and/or chemical-resistant with the priming paint of the urethane of this epoxy functional extended preparation.Notably, adopt priming paint of the present invention, observe in these improved performances one or more, and can damage any other desired properties.In addition, the urethane formulation of epoxy functional extended has lower volatile organic content (" VOC ") and but still has the viscosity of permission with this product spraying.This is significant, but because in order to obtain sprayability, other Resins, epoxy-amine priming paint needs the solvent of significant and undesirable amount usually.
Detailed Description Of The Invention
The present invention relates to comprise two components or " 2K " Resins, epoxy-amine paint base system of amine component and epoxy component.This epoxy component further comprises the urethane of epoxy functional extended.
Term as used herein " urethane of epoxy functional extended " and similar term are meant the react urethane of the epoxy functional that forms of the compound by polyepoxide that experiences chain extension and hydroxyl; In the hydroxyl that is produced by this epoxy ring-opening some react with polyisocyanates subsequently, and this polyisocyanates is used for connecting the polyepoxide molecule of this chain extension.In one embodiment of the invention, the urethane of epoxy functional extended comprises the reaction product of curable resinous polyepoxide, polyhydroxy organic compound and polyisocyanates.The unreacted epoxy groups of the urethane of this epoxy functional extended can be solidified by the amine component of paint base system.
Employed according to an embodiment of the invention curable resinous polyepoxide is usually in liquid vehicle.Operable suitable resinousness polyepoxide comprises glycidyl ether, epoxy group(ing) bakelite varnish of diglycidylether, the bis-phenol of diglycidylether, the Bisphenol F of dihydroxyphenyl propane etc.The curable resinous polyepoxide has 250 to 1500 usually, for example 300 to 550 molecular weight.This type of resinousness polyepoxide can be by the prepared in reaction of Epicholorohydrin and polyhydroxy organic compound, perhaps can buy, for example from the product of Resolution Products, perhaps from the ARALDITE strain product purchase of Ciba Specialty Chemicals with them with their EPON strain.The curable resinous polyepoxide should not need high VOC level through selecting to give the required viscosity of epoxy component, gives other desired properties in addition, and is for example flexible.
Then with polyhydroxy organic compound with resinousness polyepoxide chain extension.This polyhydroxy organic compound is polyhydroxy phenol normally, for example dihydroxyphenyl propane, Bisphenol F, trihydroxy-biphenol dimethylmethane, 4,4 '-dihydroxybiphenyl, glycol, 2,3-butanediol, tetrahydroxybutane, cresols etc.Can followingly allow resinousness polyepoxide and polyhydroxy organic compound react: with the heating of this polyepoxide, to add this polyhydroxy organic compound and catalyzer and this mixture is kept at high temperature carrying out up to reaction, for example a few hours.Can use any iodate catalyzer, for example ethyltriphenylphosphiodide iodide , or triphenyl phosphine.Reaction conditions should make from the epoxy reaction on the hydroxyl of this polyhydroxy organic compound and this resinousness polyepoxide so that with this resinousness polyepoxide chain extension.The mol ratio of polyepoxide and polyhydroxy organic compound normally 1.0: 0.5, for example 1.0: 0.2.The intermediate product of gained contains the polyepoxide of chain extension of reactive hydroxyl, has 500 to 4000 usually, for example about 980 molecular weight.This kind molecular weight is given required viscosity usually.Equally, can select to give for example viscosity and flexible of required performance polyhydroxy organic compound and resinousness polyepoxide simultaneously.
Allow intermediate product further react then with polyisocyanates.Usually, this reaction is following to be carried out: polyisocyanates is added to as above in the chilled intermediate of preparation and keep carrying out up to reaction, for example a few hours.Self-evident is that the hydroxyl on this intermediate product will form urethane bond with this isocyanate reaction.These urethane bonds are that the urethane of epoxy functional extended is given chemical-resistant.Can use any organic multiple isocyanate.For example, can use aliphatic series or aromatic diisocyanate, they comprise tolylene diisocyanate (" TDI "), MDI, IPDI, MXDI, TMXDI etc.In one embodiment of the invention, polyisocyanates is got rid of isocyanate-terminated urethane especially.The mol ratio that is used to form the polyhydroxy organic compound of intermediate product and polyisocyanates normally 1.0 to 0.5, for example 1.0 to 0.1.The product of gained, the urethane of epoxy functional extended has 1000 to 3000 usually, and for example 1500 to 2200, perhaps about 2100 molecular weight.Further will obtain higher molecular weight after the chain extension.This isocyanate-modified compound is used for the epoxy component of 2K paint base system of the present invention.The mol ratio of curable resinous polyepoxide and polyhydroxy organic compound and polyisocyanates can be 35-50: 4-12: 0.5-1.5, for example about 42: 8: 1.
Epoxy component also comprises liquid vehicle, for example organic solvent usually; The example that is fit to comprises butylacetate and Virahol, OXSOL 100, dimethylbenzene, butanols etc.Epoxy component can comprise 10 to 30%, for example the urethane of 20% epoxy functional extended and 90 to 70% solvents and/or other component as described below.In one embodiment, the solvent of epoxy component is 60% or still less.
Other component of 2K paint base system of the present invention is an amine component.This amine component should comprise a plurality of amino hydrogen atoms to carry out the curing with epoxy group(ing).Many amine are suitable for this purpose, for example aliphatic series and cycloaliphatic amines; Example comprises diethylenetriamine and Triethylenetetramine (TETA).Also can use aromatic amine, for example methylene dianiline (MDA) also can use amidoamines or polymeric amide.Amine component also comprises liquid vehicle, for example organic solvent usually; The example that is fit to comprises those that provide above.Amine component can comprise 10% to 50% amine, 90% to 50% solvent and/or other component as described below.
It will be understood by those skilled in the art that should be in use or amine component and epoxy component are mixed when using.This mixture has the work-ing life of a few hours, and it can become too sticking and can not use afterwards.Usually, 2K epoxy amine primer system of the present invention will comprise amine component and epoxy component with one to one ratio or with 0.8 to 1.5 ratio.
In one embodiment of the invention, one of in amine component and the epoxy component or both further comprise sanitas.Especially the sanitas of Shi Heing is chromate pigments such as yellow ultramarine, strontium yellow, chrome red (red chromate), zinc chromate, magnesium chromate and a baryta yellow inorganic, segmentation, uses individually or with binding substances.If add amine component to, and/or in the epoxy component, sanitas exists with 5 to 50wt% the amount that accounts for priming paint usually.
In another embodiment of the invention, one of in amine component and the epoxy component or both further comprise one or more materials.Material can comprise, for example silica, clay, talcum etc.The average particle size particle size of material changes according to selected material, but is generally 0.01 to 20 μ.Especially the clay of Shi Heing is a wilkinite.In another embodiment of the present invention, use one or more materials, in these materials one or more with polyalkoxysilane that contains at least one active hydrogen atom or siloxanes pre-reaction, this active hydrogen atom can react with the epoxy group(ing) of resinousness polyepoxide.If add in the epoxy component, this material exists with about 2.0 to 20wt% the amount that accounts for this epoxy component usually; If add in the amine component, this material exists with about 2.0 to 20wt% the amount that accounts for this amine component usually.
Other additive one of can add in this amine component and the epoxy component or both in, comprise other additive, the standard substance in pigment, rheologic additive, flowing additive and this area.When using, these additives account for 10 to 50wt% of Resins, epoxy and/or amine component usually.Amine component can further comprise catalyzer, as three (dimethyl) amino-phenol; If you are using, the requirement of this catalyzer is generally 1wt% or still less.Epoxy component can further comprise " standard " epoxide resin material, those as obtaining with their EPON strain product from Resolutia; This type of epoxide resin material can account for 10 to 50wt% of this epoxy component.
Priming paint can be coated on any suitable base material and be particularly suitable for aluminium.
The invention further relates to the urethane of aforesaid epoxy functional extended.This kind Resins, epoxy is found not only to can be used for paint base system of the present invention but also be can be used for other coating.
Unless clearly regulation is arranged in addition, and at these employed all numerical value, for example expression value, scope, amount or percentile those can be used as the front has word " approximately " to understand, even this term does not occur clearly.Any numerical range described herein is intended to be included in all subranges that wherein comprise.Plural number comprises odd number, and vice versa.Also have, as used herein term " polymer " " be meant prepolymer, oligopolymer and homopolymer and multipolymer; Prefix " is gathered " and is meant two or more.
Embodiment
Following example is intended to illustrate the present invention, in any case and should not be regarded as restriction the present invention.
Embodiment 1
The preparation of the urethane of epoxy functional extended
Table 1
| Starting material | Weight/batch of material | Wt％ | Mole |
| ARALDITE 1 GY 285 | 400 | 70.287 | 1.1940 |
| Dihydroxyphenyl propane | 50 | 8.79 | 0.2193 |
| Ethyltriphenylphosphiodide iodide | 0.40 | 0.07 | |
| Butylacetate | 113.75 | 19.99 | |
| Tolylene diisocyanate | 5.0 | 0.88 | 0.0287 |
1The Bisphenol F of epoxy functional, molecular weight 360 derives from Ciba SpecialtyChemicals.
ARALDITE GY 285 added Stainless Steel Kettles and be heated to 230 anhydrate to remove.When the water-content of measuring by Carl Fisher method less than 0.05% the time, this ARALDITE GY 285 is cooled to 205 .Add dihydroxyphenyl propane and ethyltriphenylphosphiodide iodide .With this mixture heating up to 300 and kept 4 hours, afterwards with reactor cooling to 176 .The adding butylacetate also mixed 30 minutes.The adding tolylene diisocyanate also kept 4 hours under 176 .When epoxy equivalent (weight) weight (EEW) is measured between 250 and 280, with reactor cooling to 100 and emptying.
Embodiment 2
The preparation of anti-corrosion primer
Use the urethane of epoxy functional extended
The dispersion of filler in the epoxy component of priming paint
Use high-shear with the mixture of following material slurryization together: urethane, 73 pounds of glycol monoethyl ether acetates (" EE "), 4 pounds of wilkinites of the epoxy functional extended of preparation among 358 pounds of embodiment 1.Continue to mix 15 minutes.Under agitation add the urethane resin of 431 pounds of strontium yellows, 76 pounds of titanium dioxide, 25 pounds of Amsco solvent EE and 131 pounds of epoxy functional extended.Allow whole mixture by medium grinder and be subjected to grinding reduction ratio up to reaching 7.After grinding, transfer this mixture rare with the urethane resin of 108 pounds of epoxy functional extended, 50 pounds of Amsco solvent EE and 40 pounds of pimelinketone.
The curing solution of this mixture is prepared as follows: 179 pounds of polymeric amide (EPICURE 3115, the solidifying agent that is purchased from Resolutia), 77 pounds of toluene, 243 pounds of butanols and 184 pounds of aminosilanes are merged.The proportioning of above-mentioned two components is that the urethane of 1.5 parts of epoxy functional extended is than 1 part of amine curing solution by volume.
By in sealed can, shake component mixed and use conventional pressure-pot equipment or HVLP equipment by spray coating on aluminum test panels.Coating thickness is the 0.6-0.9 mil.Estimate the flexible of this priming paint on the aluminium sheet by this compound being sprayed to 20 mil thick.Solidified 24 hours with air-dry 14 days of this plate or under 150 .This plate is placed on the GE impact tester.When as above testing, above-mentioned priming paint shows the elongation greater than 20%.This priming paint also shows good oil resistant and fuel, can not turn white and show good adhesivity.
The dispersion of filler in the amine component of product
Under agitation 185 pounds of polymeric amide, 165 pounds of butanols, 360 pounds of strontium yellows, 18 pounds of carbon blacks, 12 pounds of extinction powders, 108 pounds of dimethylbenzene, 294 pounds of silicon-dioxide are merged.Allow whole mixture by medium grinder and be subjected to grinding reduction ratio up to reaching 6+.Transfer this material rare with other 70 pounds of butanols.
Activator component is prepared as follows: with 414 pounds of OXSOL 100 (solvent that is purchased from Isle Chem), 36 pounds of EPON 828 (Resins, epoxy that is purchased from Resolutia), 514 pounds of urethane resin and 9 pounds of epoxy radicals silicone hydrides that are purchased with SILQUESTA-187 from Witco according to the epoxy functional extended of embodiment 1 preparation.Stirring whole mixture with the high-speed stirring oar will maintain under 90 simultaneously.
Can this activator component be combined with amine component by 1: 1 volume ratio.When by the GE shock measurement, the elongation of this priming paint is greater than 20%.On the contrary, when activator only is made of Epon 828, priming paint flexible less than 10%.This priming paint also shows good oil resistant and fuel, can not turn white and show good adhesivity.
Though described particular of the present invention above for purpose of explanation, it is conspicuous under the situation of the present invention that does not break away from defined in the appended claims details of the present invention being made many changes for a person skilled in the art.
Claims (25)
1. two component epoxy amine paint base systems, it comprises:
Amine component; With
Epoxy component, wherein this epoxy component comprises the urethane of epoxy functional extended.
2. the system of claim 1, wherein the urethane of this epoxy functional extended comprises the reaction product of following material:
A) curable resinous polyepoxide;
B) polyhydroxy organic compound; With
C) polyisocyanates.
3. the system of claim 2, wherein the molecular weight of this resinousness polyepoxide is 360 to 550.
4. the system of claim 2, wherein the molecular weight of the urethane of this epoxy functional extended is 1500 to 2200.
5. the system of claim 2, wherein this curable resinous polyepoxide comprises the diglycidylether of bis-phenol.
6. the system of claim 5, wherein this bis-phenol is a Bisphenol F.
7. the system of claim 2, wherein this polyhydroxy organic compound is a dihydroxyphenyl propane.
8. the system of claim 2, wherein this polyisocyanates is a tolylene diisocyanate.
9. the mol ratio of the system of claim 2, wherein a: b: c is 35-50: 4-12: 0.5-1.5.
10. the system of claim 2, wherein this curable resinous polyepoxide comprises the diglycidylether of Bisphenol F, this polyhydroxy organic compound comprises dihydroxyphenyl propane and this polyisocyanates comprises tolylene diisocyanate, and the ratio of a: b: c is 35-50: 4-12: 0.5-1.5.
11. the system of claim 1, wherein this amine component comprises aliphatic amine.
12. the system of claim 1, wherein this amine component and/or epoxy component further comprise one or more sanitass, and/or one or more materials, and/or their mixture.
13. the system of claim 12, wherein this sanitas comprises chromic salt.
14. the system of claim 13, wherein this chromic salt comprises strontium yellow.
15. the system of claim 12, wherein this material comprises the binding substances of silica and clay.
16. the system of claim 15, wherein this clay comprises wilkinite.
17. the urethane of epoxy functional extended, it comprises the reaction product of following material:
A) curable resinous polyepoxide;
B) polyhydroxy organic compound; With
C) polyisocyanates.
18. the urethane of claim 17, wherein the molecular weight of this resinousness polyepoxide is 360 to 550.
19. the urethane of claim 17, wherein the molecular weight of the urethane of this epoxy functional extended is 1500 to 2200.
20. the urethane of claim 17, wherein this curable resinous polyepoxide comprises the diglycidylether of bis-phenol.
21. the urethane of claim 20, wherein this bis-phenol is a Bisphenol F.
22. the urethane of claim 17, wherein this polyhydroxy organic compound is a dihydroxyphenyl propane.
23. the urethane of claim 17, wherein this polyisocyanates is a tolylene diisocyanate.
24. the ratio of the urethane of claim 17, wherein a: b: c is 35-50: 4-12: 0.5-1.5.
25. the urethane of claim 17, wherein this curable resinous polyepoxide comprises the diglycidylether of Bisphenol F, this polyhydroxy organic compound comprises dihydroxyphenyl propane and this polyisocyanates comprises tolylene diisocyanate, and the ratio of a: b: c is 35-50: 4-12: 0.5-1.5.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/879,564 US20050288456A1 (en) | 2004-06-28 | 2004-06-28 | Flexible, impact resistant primer |
| US10/879,564 | 2004-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1976968A true CN1976968A (en) | 2007-06-06 |
Family
ID=35506874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2005800215604A Pending CN1976968A (en) | 2004-06-28 | 2005-06-23 | Flexible, impact resistant primer |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20050288456A1 (en) |
| EP (1) | EP1765905B1 (en) |
| JP (1) | JP2008501853A (en) |
| KR (1) | KR100849266B1 (en) |
| CN (1) | CN1976968A (en) |
| AT (1) | ATE414727T1 (en) |
| AU (1) | AU2005280622B2 (en) |
| CA (1) | CA2577694A1 (en) |
| DE (1) | DE602005011139D1 (en) |
| DK (1) | DK1765905T3 (en) |
| ES (1) | ES2317331T3 (en) |
| IL (1) | IL180084A0 (en) |
| RU (1) | RU2346968C2 (en) |
| UA (1) | UA82957C2 (en) |
| WO (1) | WO2006025928A2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109722148A (en) * | 2019-01-03 | 2019-05-07 | 珠海市威旗防腐科技股份有限公司 | A kind of thixotropic solventless epoxy coating and preparation method thereof |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7498384B2 (en) * | 2005-02-04 | 2009-03-03 | Ppg Industries Ohio, Inc. | Multi-component epoxy-amine primer systems comprising a polythioether |
| US8178475B2 (en) | 2006-06-09 | 2012-05-15 | M-I L.L.C | Surfactant materials and coatings for weighting agents for use in oil based drilling fluids |
| US7727938B2 (en) * | 2006-06-09 | 2010-06-01 | M-I L.L.C. | Non-aqueous gels for consolidating and stabilizing wellbore formations |
| US7786052B2 (en) * | 2006-06-09 | 2010-08-31 | M-I L.L.C. | Hydrophobically modified fluid loss additives and viscosifier products |
| US7569163B2 (en) * | 2007-03-16 | 2009-08-04 | Prc Desoto International, Inc. | Polythioether amine resins and compositions comprising same |
| US8414981B2 (en) * | 2007-08-17 | 2013-04-09 | Prc Desoto International, Inc. | Multilayer coatings suitable for aerospace applications |
| EP2470609B1 (en) * | 2009-08-27 | 2013-07-24 | Akzo Nobel Coatings International B.V. | Use of a catalyst in a base coating to improve the strippability of subsequent coatings |
| US11932795B2 (en) | 2020-06-03 | 2024-03-19 | Ecolab Usa Inc. | Aromatic amine epoxide adducts for corrosion inhibition |
| US11939553B2 (en) | 2020-06-03 | 2024-03-26 | Ecolab Usa Inc. | Non-caustic cleaning compositions and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3660523A (en) * | 1970-02-25 | 1972-05-02 | Desoto Inc | Aluminum primer containing epoxide resin and isocyanate terminated urethane prepolymer |
| US4075153A (en) * | 1976-10-01 | 1978-02-21 | Desoto, Inc. | Corrosion-resistant epoxy-amine chromate-containing primers |
| US4520144A (en) * | 1984-02-06 | 1985-05-28 | Desoto, Inc. | Polydimethylsiloxane-modified polyepoxides |
| US5204385A (en) * | 1990-11-27 | 1993-04-20 | Reichhold Chemicals, Inc. | Water reducible epoxy resin curing agent |
| JPH0860047A (en) * | 1994-08-17 | 1996-03-05 | Kansai Paint Co Ltd | Cationic electrodeposition coating composition |
| GB9620246D0 (en) * | 1996-09-26 | 1996-11-13 | Courtaulds Plc | Improvements in or relating to coating substrates |
| US7169862B2 (en) * | 2002-10-04 | 2007-01-30 | E. I. Du Pont De Nemours And Company | Solvent-borne two component modified epoxy/polyamine coating composition |
-
2004
- 2004-06-28 US US10/879,564 patent/US20050288456A1/en not_active Abandoned
-
2005
- 2005-06-23 ES ES05812010T patent/ES2317331T3/en active Active
- 2005-06-23 CN CNA2005800215604A patent/CN1976968A/en active Pending
- 2005-06-23 DK DK05812010T patent/DK1765905T3/en active
- 2005-06-23 AU AU2005280622A patent/AU2005280622B2/en not_active Ceased
- 2005-06-23 JP JP2007527819A patent/JP2008501853A/en not_active Withdrawn
- 2005-06-23 KR KR1020067027723A patent/KR100849266B1/en not_active IP Right Cessation
- 2005-06-23 DE DE602005011139T patent/DE602005011139D1/en not_active Expired - Fee Related
- 2005-06-23 RU RU2007103153/04A patent/RU2346968C2/en not_active IP Right Cessation
- 2005-06-23 EP EP05812010A patent/EP1765905B1/en not_active Not-in-force
- 2005-06-23 UA UAA200700857A patent/UA82957C2/en unknown
- 2005-06-23 WO PCT/US2005/022593 patent/WO2006025928A2/en active Application Filing
- 2005-06-23 AT AT05812010T patent/ATE414727T1/en not_active IP Right Cessation
- 2005-06-23 CA CA002577694A patent/CA2577694A1/en not_active Abandoned
-
2006
- 2006-12-14 IL IL180084A patent/IL180084A0/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109722148A (en) * | 2019-01-03 | 2019-05-07 | 珠海市威旗防腐科技股份有限公司 | A kind of thixotropic solventless epoxy coating and preparation method thereof |
| CN109722148B (en) * | 2019-01-03 | 2020-12-22 | 珠海市威旗防腐科技股份有限公司 | Thixotropic solvent-free epoxy coating and preparation method thereof |
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| Publication number | Publication date |
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| IL180084A0 (en) | 2007-05-15 |
| EP1765905B1 (en) | 2008-11-19 |
| DK1765905T3 (en) | 2009-01-19 |
| EP1765905A2 (en) | 2007-03-28 |
| KR100849266B1 (en) | 2008-07-29 |
| AU2005280622A1 (en) | 2006-03-09 |
| CA2577694A1 (en) | 2006-03-09 |
| WO2006025928A2 (en) | 2006-03-09 |
| WO2006025928A3 (en) | 2006-05-04 |
| UA82957C2 (en) | 2008-05-26 |
| DE602005011139D1 (en) | 2009-01-02 |
| AU2005280622B2 (en) | 2008-04-17 |
| JP2008501853A (en) | 2008-01-24 |
| RU2346968C2 (en) | 2009-02-20 |
| ATE414727T1 (en) | 2008-12-15 |
| RU2007103153A (en) | 2008-08-10 |
| US20050288456A1 (en) | 2005-12-29 |
| ES2317331T3 (en) | 2009-04-16 |
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